HCID 10531733, compound → HCID 21182877, compound

HRID 1387086Notes

Reaction equation

HRID 1387086 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][C:33]=1[CH2:34][N:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1)[CH2:5][C:6]1[C:7]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][C:8]=2[S:9][C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:13][CH:12]=1.C([Li])CCC>C1COCC1>[CH3:30][O:29][C:26]1[CH:27]=[CH:28][C:7]2[C:6]([CH2:5][C:4]3[CH:3]=[CH:2][C:33]([CH2:34][N:35]4[CH2:39][CH2:38][CH2:37][CH2:36]4)=[CH:32][CH:31]=3)=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][N:20]4[CH2:21][CH2:22][CH2:23][CH2:24]4)=[CH:13][CH:12]=3)[S:9][C:8]=2[CH:25]=1

Participants

4

Reactant 2

HCID 10531733HCID 10531733, compoundHCID 178418339Butyllithium

Product 1

HCID 21182877HCID 21182877, compoundYield 41.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-60 °C

Procedure

To a solution of 3-[3-bromo-4-[(1-pyrrolidinyl)methyl]benzyl]-6-methoxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene (100 mg, 0.16 mmol) in THF (2 mL) at −60° C. under argon was added a solution of n-butyllithium in hexanes (1.6 M, 0.2 mL) and the mixture was stirred at −60° C. for 20 min. The reaction was quenched with 0.5 mL of MeOH and allowed to warm up to ambient temperature. The mixture was then concentrated under reduced pressure and fractionated by flash chromatography with Et3N:MeOH:EtOAc (3:3:94) to afford the product (35 mg, 40%).

Workup

  1. customThe reaction was quenched with 0.5 mL of MeOH
  2. temperatureto warm up to ambient temperature
  3. concentrationThe mixture was then concentrated under reduced pressure and fractionated by flash chromatography with Et3N:MeOH:EtOAc (3:3:94)

Sources & evidence

ORD record
ord-bcc2cf9238e14313a2a59ebc02ee3cb8
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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